EP0912527A1

EP0912527A1 - Substituted aromatic carbonyl compounds and their derivatives

Info

Publication number: EP0912527A1
Application number: EP97930469A
Authority: EP
Inventors: Roland Andree; Mark Wilhelm Drewes; Wilhelm Haas; Andreas Lender; Karl-Heinz Linker; Otto Schallner; Markus Dollinger
Original assignee: Bayer AG
Current assignee: Bayer AG
Priority date: 1996-07-11
Filing date: 1997-07-01
Publication date: 1999-05-06
Also published as: AU3441297A; WO1998002422A1; CA2260201A1; BR9710238A; IL127802A0; DE19627901A1; JP2000514805A

Abstract

New substituted aromatic carbonyl compounds and their derivatives have the general formula (I), in which Q stands for oxygen, sulphur or imino (NH); R1 stands for hydrogen or halogen; and R2 stands for the group -A1-A2-A3, in which A?1, A2 and A3¿ have the meanings given in the description. Also disclosed are a process for preparing the same and their use as herbicides.

Description

Substituted aromatic carbonyi compounds and their derivatives

The invention relates to new substituted aromatic carbonyiver compounds and their derivatives, processes for their preparation and their use as herbicides

Some substituted aromatic carbonyl compounds with heterocyclyl groups bonded via nitrogen are already known (cf. DE-2 102 848, DE-2 1 19 260, DE-2 166 456, DE-2 342 934). However, nothing is known about the herbicidal activity of these compounds

There have now been new substituted aromatic carbonyi compounds and their

Derivatives of the general formula (I)

in which

Q represents oxygen, sulfur or imino (NH),

R represents hydrogen or halogen,

R> 2 represents the grouping below,

-A ^] -A ² -A ³

wherein for a single bond, for oxygen, sulfur, -SO-, -SO ₂ -, -CO- or the grouping -NR ⁴ -, wherein R ^{4 is} hydrogen, hydroxy or a radical of the series alkyl, alkoxy, aryl, alkyl - stands for sulfonyl or arylsulfonyl, A ¹ furthermore represents an optionally substituted radical from the series alkanediyl, alkenediyi, alkindiyl, cycloalkanediyl, cycloalkenediyl or arenediyl,

A ^{2 represents} a single bond, represents oxygen, sulfur, -SO-, -SO -, -, -CO- or the group -NR ⁵ -, in which R ^{5 represents} hydrogen,

Hydroxyl or a radical of the series alkyl, aryl, alkoxy, alkylsulfonyl or arylsulfonyl,

A ^~ furthermore represents an optionally substituted radical from the series alkanediyl, alkenediyi, alkindiyl, cycloalkanediyl, cycloalkenediyl or arenediyl, and

A for hydrogen, hydroxy, amino, cyano, isocyano, thiocyanato, nitro, carboxy, carbamoyl, thiocarbamoyl, sulfo, chlorosulfonyl, halogen or for an optionally substituted radical from the series alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, Alkoxycarbonyl, dialkoxy (thio) phosphoryl, alkenyl, alkenyloxy, alkenylamino, alkylidene amino, alkenyloxycarbonyl, alkynyl, alkynyloxy, alkynylamino, alkynyloxycarbonyl, cycloalkyl, cycloalkyloxy, cycloalkylalkyl, cycloalkylalkoxy, cycloalkylidenoxycarbonyl, cycloalkyloxycarbonyl, cycloalkyloxycarbonyl, cycloalkyloxycarbonyl, cycloalkyloxycarbonyl, cycloalkyloxycarbonyl, cycloalkyloxyoxycyclo Aryloxy, arylalkyl, arylalkoxy, aryloxycarbonyl, arylalkoxycarbonyl, heterocyclyl, heterocyclylalkyl, heterocyclylalkoxy or heterocyclylalkoxycarbonyl,

R ^{3 represents} hydrogen, hydroxy, mercapto, amino (in which case Q does not represent sulfur) or an optionally substituted radical from the series alkyl, alkoxy, alkylthio or alkylamino, and

Z represents an optionally substituted monocyclic or bicyclic, saturated or unsaturated radical from the heterocyclyl series (exception: piperazinyl), heterocyclylamino or heterocyclylimino,

with the exception of the previously known compounds 5-chloro-4- (1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl) -2-methoxy-benzoic acid ethyl ester and 5-chloro-4- (l, 3-dihydro-l, 3-dioxo-2H-isoindol-2-yl) -2-methoxy-benzoic acid methyl ester (both known from DE-2 102 848, DE-2 1 19 260 and DE-2 166 456) and 8-chloro-3- (2-chloro-5-methoxy-4-methoxycarbonyl-phenyl) -3,4-dιhydro-5- methoxy-chιnazolιn-6-carbon-acidic methyl ester (known from Tetrahedron Lett 34 (1993), 1889-1892)

found

The new substituted aromatic carbonyi compounds and their derivatives of the general formula (I) are obtained if substituted aromatic nitylenes of the general formula (II)

in which

R, R and Z have the meanings given above,

with water, hydrogen sulfide or ammonia, if appropriate in the presence of reaction auxiliaries, and the resulting substituted aromatic carboxylic acids or their derivatives of the general formula (Ia)

in which

Q, R. 1, R r 2 ^~ and Z have the meanings given above, optionally converted into substituted aromatic carbonyi compounds or their derivatives according to the above definition of the compounds of formula (I) by customary methods

The new substituted aromatic carbonyi compounds of the general formula (I) are notable for their strong herbicidal activity

In the definitions, the saturated or unsaturated hydrocarbon chains, such as alkyl, alkanediyl, alkenyl or alkynyl - also in combination with heteroatoms, such as in alkoxy, alkylthio or alkylamino - are each straight-chain or branched

Halogen generally represents fluorine, chlorine, bromine or iodine, preferably

Fluorine, chlorine or bromine, especially for fluorine or chlorine

The invention preferably relates to compounds of the formula (1) in which

Q represents oxygen, sulfur or imino (NH),

R ^{1 represents} hydrogen, fluorine, chlorine or bromine,

R ^{2 represents} the grouping below,

-A'-A ² -A ³

in which

A ^{1 represents} a single bond, represents oxygen, sulfur, -SO-, -SO ₂ -, -CO- or the group -NR ⁴ -, in which R ^{4 represents} hydrogen,

Is hydroxyl or a radical of the series C, -C ₄ -alkyl, C _r C ₄ -alkoxy, phenyl, C, -C ₄ -alkylsulfonyl or phenylsulfonyl,

A ¹ furthermore represents a substituted each optionally substituted by fluorine or chlorine radical from the group C _r C ₆ - alkanediyl, C ₂ -C ₆ - Alkendiyi, C ₂ - C ₆ alkynediyl, C -C ₆ -cycloalkanediyl, C _r C ₆ - Cycloalkenediyl or

Phenyl is A ^{2 represents} a single bond, represents oxygen, sulfur, -SO-, -SO -, -, -CO- or the grouping -NR ⁵ -, wherein R ^{5 represents} hydrogen, hydroxy or a radical of the series C, -C ₄ -Alkyl, CC ₄ -alkoxy, phenyl, C _] -C ₄ -alkylsulfonyl or phenylsulfonyl,

A ² continues for a each is optionally substituted by fluorine or chlorine radical from the series C, -C ₆ -Alkandιyl, C ₂ -C ₆ -Alkendιyl, C, - C ₆ alkynediyl, C ₆ -C -Cycloalkandtyl, C ₃ -C ₆ -Cycloalkendιyl or phenyl is,

A ¹ for hydrogen, hydroxy, amino, cyano, isocyano, thiocyanato, nitro, carboxy, carbamoyl, thiocarbamoyl, sulfo, chlorosulfonyl,

Halogen or for a radical of the series alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, alkoxycarbonyl or dialalkoxy (thιo) phosphoryl which is optionally substituted by halogen, C, - C ₄ -alkoxy or C, -C ₄ -alkoxιmιno each has 1 to 6 carbon atoms in the alkyl groups,

A ³ furthermore represents an optionally substituted by halogen radical from the series alkenyl, alkenyloxy, alkenylamino, alkylene amine, alkenyloxycarbonyl, alkynyl, alkynyl oxy, alkynylamino or alkynyloxycarbonyl, each having 2 to 6 carbon atoms in the alkenyl, alkylene or alkynyl groups stands,

A "further for a radical of the series cycloalkyl, cycloalkyloxy, cycloalkylalkyl, cycloalkylalkoxy, cycloalky denamino, cycloalkyloxycarbonyl or optionally substituted by halogen, cyano, carboxy, C ₁ -C ₄ alkyl and / or C _] -C ₄ alkoxycarbonyl Cycloalkylalkoxycarbonyl each having 3 to 6 carbon atoms in the cycloalkyl groups and optionally 1 to 4 carbon atoms in the alkyl groups,

A ³ further for each optionally by nitro, cyano, carboxy, halogen, C _r C ₄ alkyl, C _r C ₄ haloalkyl, C, -C ₄ alkyloxy, C _] -C ₄ haloalkyloxy and / or C, -C ₄ alkoxy-carbonyl substituted radical of the series phenyl, phenyl oxy, phenyl-C _r C ₄ -alkyl, phenyl-C, -C ₄ -alkoxy, phenyl oxy carbonyl or phenyl-C, -C ₄ -alkoxy - carbonyl, (in each case optionally completely or partly hydrogenated) pyrrolyl, pyrazolyl, imidazolyl, triazolyl, furyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, Isothiazoiyl, oxadiazolyl, thiadiazolyl, Pyπ- dinyl, pyrimidinyl, triazinyl, pyrazolyl-C _r C ₄ alkyl , FuryI-C _r C ₄ -alkyl, thienyl-C, -C ₄ -alkyl, oxazolyl-C, -C ₄ -alkyl, isoxazole-C, -C ₄ -alkyi, thiazole-C _r C ₄ -alkyl, pyridinyl-C, -C ₄ -alkyl, pyrimidinyl-C _r C ₄ -alkyl, pyrazolylmethoxy, furylmethoxy, represents perhydropyranylmethoxy or pyridylmethoxy,

R 'represents hydrogen, hydroxy, mercapto, amino (in which case Q does not represent sulfur) or one in each case optionally by hydroxy,

Cyano, halogen, C _] -C ₄ alkoxy or C _j -C ₄ alkoxy carbonyl substituted

The rest of the series alkyl, alkoxy, alkylthio or alkylamino, each with 1 to

6 carbon atoms in the alkyl groups, and

Z represents a respective monocyclic or bicyclic, saturated or unsaturated radical from the heterocyclyl series (except piperazinyl), heterocycliclamino or heterocyclylimino, each with 2 to 6 carbon atoms and 1 to 4 nitrogen atoms in the heterocyclic ring system, which optionally also contains an oxygen or Contains sulfur atom and / or optionally up to three groups from the series -CO-, -CS-, -SO- and / or SO ₂ -, and which is optionally substituted by one or more groups from the series nitro, hydroxy, amino, Cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, C, -C -alkyl (which in turn is optionally substituted by halogen or C, -C ₄ -alkoxy), C ₂ -C ₆ -alkenyl or C ₂ -C ₆ -alkynyl ( which in turn are optionally substituted by halogen), C, -C ₆ alkoxy or C _r C ₆ -

Alkoxycarbonyl (which in turn are each optionally substituted by halogen or C 1 -C ₄ -alkoxy), C ₂ -C ₆ alkenyloxy or C- _> C ₆ -alkynyloxy (which in turn are each optionally substituted by halogen), C , -C ₆ alkylthio, C ₂ -C ₆ alkenylthio or C ₂ -C ₆ alkynylthio (which in turn are each optionally substituted by halogen),

C _r C ₆ -alkylamino or di- (C, -C ₄ -alkyl) -amino, CC ₆ -cycloalkyl or CC ₆ -cycloalkyl-C, -C ₄ -alkyl (which in turn in each case optionally by halogen and / or C, -C ₄ alkyl are substituted), phenyl, phenoxy, phenylthio, phenyl sulfinyl, phenylsulfonyl or phenylamino (which in turn are each optionally substituted by nitro, cyano, halogen, C, -C ₄ alkyl, C, -C ₄ - Haloalkyl, C, -C ₄ -alkyloxy, C, -C ₄ -Ha! Ogenalkyloxy and / or C, -C ₄ - alkoxy-carbonyl are substituted),

where the previously known compounds 5-chloro-4- (1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl) -2-methoxy-benzoic acid ethyl ester and 5-chloro-4- (l , 3-dihydro-l, 3-di-oxo-2H-isoιndol-2-yl) -2-methoxy-benzoic acid methyl ester (both known from DE-

2 102 848, DE-2 1 19 260 and DE-2 166 456) and 8-chloro-3- (2-chloro-5-methoxy-4-methoxycarbonylphenyl) -3,4-dihydro-5- methoxy-quinazoline-6-carboxylic acid methyl ester (known from Tetrahedron Lett 34 (1993), 1889-1892) are excluded by discriminators

The invention relates in particular to compounds of the formula (I) in which

Q represents oxygen, sulfur or imino (NH),

R ^{1 represents} hydrogen, fluorine or chlorine,

R ^{2 represents} the grouping below,

-A'-A ² -A ³

in which

A ¹ for a single bond, for oxygen, sulfur, -SO-, -SO -, -,

-CO- or the grouping -NR ⁴ -, where R ^{4 is} hydrogen,

Hydroxyl or a radical of the series methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methyl sulfonyl or ethyl sulfonyl,

A ¹ furthermore for a radical of the series methylene, ethane-l, l-diyl, ethane-1,2-diyl, propane-l, l-diyl, propane-l, 2-diyl, propane-l, 3-diyl, Ethen-1, 2-diyl, propene-1,2-diyl, propene-1,3-diyl, ethyne-1,2-diyl, propyne-1,2-diyl or propyne-1,3-diyl,

A ^{2 represents} a single bond, represents oxygen, sulfur, -SO-, -SO -, -CO- or the grouping -NR ⁵ -, in which R ^{5 represents} hydrogen, Hydroxyl or a radical of the series methyl, ethyl, n- or l-propyl, methoxy, ethoxy, n- or l-propoxy, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl or phenyl sulfonyl,

A ² furthermore for a radical of the series methylene, ethane-1, 1-dιyl, ethane-1, 2-diyl, propane-l, l-dιyl, propane-1,2-diyl, propane-1,3-diyl, Ethen

1,2-diyl, propene-1,2-diyl, propene-1,3-diyl, ethyne-1,2-diyl, propyne-1,2-diyl or propyne-1,3-diyl,

A ¹ for hydrogen, hydroxyl, amino, cyano, nitro, carboxy, carbamoyl, sulfo, fluorine, chlorine, bromine, for each optionally by fluorine, chlorine, methoxy, ethoxy, methoximino or

Ethoximino substituted radical of the series methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-, l-, s- or t-pentyl, methoxy, ethoxy, n- or i -Propoxy, n-, i-, s- or t-butoxy, n-, i-, s- or t-pentyloxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t -Butylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl,

Methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, methylamino, ethylamino, n- or l-propylamino, n-, I-, s- or t-butylamino, dimethylamino, diethylamino, methoxycarbonyl, ethoxycarbonyl, n - or l-propoxycarbonyl, dimethoxyphosphoryl, diethoxyphosphoryl, dipropoxyphosphoryl or dnsopropoxyphosphoryl,

A 'furthermore for a radical of the series propenyl, butenyl, propenyloxy which is optionally substituted by fluorine or chlorine,

Butenyloxy, propenylarmno, butenylamino, propylidene amino, butylidene amino, propenyloxycarbonyl, butenyloxy carbonyl, propynyl,

Butynyl, propynyloxy, butmyloxy, propynylam o, butynylamino, propynyloxycarbonyl or butynyloxycarbonyl,

A ³ furthermore for one each optionally by fluorine, chlorine,

Cyano, carboxy, methyl, ethyl, n- or l-propyl, methoxycarbonyl or ethoxycarbonyl substituted radical from the cyclopropyl series,

Cyclobutyl, cyclopentyl, cyclohexyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclopropyl methoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy, cyclopentylideneamino, cyclohexyhdenamino, cyclopentyloxycarbonyl, cyclohexyloxycarbonyl, cyclopentylmethoxycarbonyl or cyclohexylmethoxycarbonyl,

A ¹ furthermore for one in each case optionally by nitro, cyano,

Carboxy, fluorine, chlorine, bromine, methyl, ethyl, n- or l-propyl, Tπ- fluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, Tπfluorm ethoxy, methoxycarbonyl and / or ethoxycarbonyl substituted radical of the phenyl series, Phenyloxy, benzyl phenylethyl, benzyloxy, phenyloxycarbonyl, benzyloxycarbonyl, (each optionally wholly or partly hydrogenated) pyrrolyl, pyrazolyl, imidazolyl, tπazolyl, furyl, thienyl, oxazolyl, isoxazolyl, thiazo-lyl, isothiazolyl, oxadiazolyl, thiadidinylyl, thiadidinylolthiadinyladi, piidiazinyl Pyrazolylmethyl, furylmethyl, thienylmethyl, oxazolylmethyl, isoxazolmethyl, thiazolmethyl, pyπdinylmethyl, pyπmidinylmethyl, pyrazolylmethoxy, furylmethoxy or pyπdylmethoxy,

R ^{3 represents} hydrogen, hydroxyl, mercapto, amino (in which case Q does not represent sulfur) or a radical of the series methyl, ethyl, n- which is optionally substituted by hydroxyl, cyano, fluorine, chlorine, methoxy, ethoxy, methoxycarbonyl or ethoxycarbonyl. or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylamino, ethylamino, n- or l-propylamino, and

Z stands for a monocychic or bicyclic, saturated or unsaturated residue of the heterocyclyl series (exception: piperazinyl), heterocycliclamino or heterocyclylimino, each with 2 to 5 carbon atoms and 1 to 3 nitrogen atoms in the heterocyclic ring system, which optionally also contains an oxygen or Contains sulfur atom and / or optionally up to two groups from the series -CO-, -CS-, -SO- and / or SO -, -, which is optionally substituted by one or more groupings from the series nitro, hydroxy, amino , Cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, methyl, ethyl, n- or l-propyl, n-, 1-, s- or t-butyl, (which in turn may be replaced by fluorine, chlorine, methoxy or Are substituted ethoxy), Propenyl, butenyl, propynyl or butynyl (which in turn are each optionally substituted by fluorine or chlorine), methoxy, ethoxy, n- or i-propoxy, n-, 1-, s- or t-butoxy, methoxycarbonyl or ethoxycarbonyl ( which in turn are optionally substituted by fluorine, chlorine, methoxy or ethoxy), propenyloxy, butenyloxy, propynyloxy or butynyloxy (which in turn are optionally substituted by fluorine or chloro), methylthio, ethylthio, n- or i-propylthio, n- , i- s- or t-butylthio, propenylthio, butenylthio, propynylthio or butynylthio (which in turn are each optionally substituted by fluorine or chlorine), methylamino, ethylamino, n- or i-propylamino, n-, I-, s - or t-butylamino, dimethylamino or diethylamino, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl (which in turn in each case optionally by fluorine, chlorine, methyl, ethyl, n- or l-propyl are substituted) phenyl, phenoxy, phenylthio, phenylsulfinyl, phenylsulfonyl or phenylamino (which in turn in each case optionally by nitro, cyano, fluorine, chloro, bromine, methyl, ethyl, n- or l-propyl, t-fluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, tifluoromethoxy, methoxycarbonyl or ethoxycarbonyl are substituted),

where the previously known compounds 5-chloro-4- (l, 3-dιhydro-l, 3-dιoxo-2H-ιsoιn- doI-2-yl) -2-methoxy-benzoic acid ethyl ester and 5-chloro-4- (l , 3-dιhydro-l, 3-dιoxo- 2H-ιsoιndol-2-yI) -2-methoxy-benzoic acid methyl ester (both known from DE-2 102 848, DE-2 1 19 260 and DE-2 166 456) as well as 8-chloro-3- (2-chloro-5-methoxy-4-methoxycarbonylphenyl) -3,4-dihydro-5-methoxychιnazohn-6-carboxylic acid methyl ester (known from Tetrahedron Lett 34 (1993 ), 1889-1892) are excluded by discla- mer

Z in the general formula (I) in particular represents the heterocyclic groups listed below,

(Z ¹ ) (Z ² ) (Z ³ ) R '

, .Q I

& N ^" R '. Q'

^" NN ^" ^: N w \ /

R NS r ^x N = N

(Z ") (Z ⁵ ) (Z °

(z ⁷ ) (Z ° (Z ⁹ )

(z ¹⁰ ) (z ¹¹ ) (z ¹² )

15,

(z ¹³ ) (Z ¹⁴ ) (Z

(z ¹⁶ ) (z ¹⁷ ) (Z '

(Z ²² ) (Z ²³ ) (Z ²⁴ )

where each

Q ¹ for a grouping from the series -CO-, -CS-, -CH ₂ -, -CH (OH) -, -CHCl-, -CHBr-, -C (= CH ₂ ) -, -C (= CHF ) -, -C (= CF ₂ ) -, -C (= CHCI) -, -C (= CHBr) -, -C (= CHOCHF ₂ ) -, -C (= CHOCF ₃ ) -, -C (= CHOCH ₂ CF ₃ ) - stands,

Q ² for oxygen, sulfur or a group from the series -CO-, -CS-, -CH ₂ -, -CHF-, -CF ₂ -, -CHCl-, -CHBr-, -CHOCHF ₂ -, -CHOCF -, -CHOCH ₂ CF ₃ -,

R ⁶ for hydrogen, amino, nitro, cyano, carboxy, carbamoyl, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, cyclopropyl, difluoromethyl, Tπ-fluoromethyl, chlorodifluoromethyl, methoxy, ethoxy, n- or i -Propoxy, difluoromethoxy, tπfluoromethoxy, chlorodifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, difluoromethylthio, tifluoromethylthio, chlorodifluoromethylthio, methylammo, ethyl ino, n- or l-propylamino, dimethylamino, diethylamino, diethylamino, diethylamino, diethylamino, diethylamino, diethylamino, diethylamino, diethylamino, diethylamino, diethylamino, diethylamino, diethylamino, diethylamino, diethylamino, diethylamino, diethylamino, diethylamino, diethylamino Ethoxycarbonyl stands, and

R represents hydrogen, hydroxy, amino, cyano, methyl, ethyl, n- or i-propyl,

Difluoromethyl, methoxy, ethoxy, n- or i-propoxy,

or where appropriate two adjacent groups - R ⁶ and R ⁶ or R ⁷ and R ⁷ or R ⁶ and R ⁷ - together for each optionally substituted by fluorine, chlorine, bromine, methyl, ethyl, n- or l-propyl and optionally by

Oxygen, sulfur or a group from the series -SO-, SO ₂ -, -N (CH ₃ ) - or N (C-, H ₅ ) - at the beginning (or at the end) or within the hydrocarbon chain with interrupted alkanediyl or alkendiyi each have up to 4 carbon atoms

The general or preferred radical definitions given above apply both to the end products of the formula (I) and correspondingly to the starting materials or intermediates required in each case for production. These radical definitions can be combined with one another as desired, that is to say also between the specified ranges of preferred compounds

Examples of the compounds of formula (I) according to the invention are listed in the groups below Group 1

CH,

Q, R, R ^~ and R ^" have the meanings given in the list below

Group 2

1 "^

Q, R, R ^~ and R have, for example, the meanings given above in Group 1.

sip

Q, R, R and R 'have, for example, the meanings given above in Group 1.

Group 4

Q, R ¹ , R ² and R ³ have, for example, the meanings given above in Group 1. Group 5

Q, R ^! , R ² and R ³ have, for example, the meanings given above in Group

Group 6

Q, R, R ^~ and R ¹ have, for example, those given above in Group 1

Meanings

Group 7

Q, R, R "and R ¹ have, for example, the meanings given above in Group 1 Group 8

Q, R ¹ , R ² and R ¹ have, for example, those given above in Group 1

Meanings

Group 9

Q, R, R ~ and R ^J have, for example, those given in Group 1 above

Meanings.

Group 10

0, R ¹ , R ² and R ^J have, for example, the meanings given above in Group 1. Group 11

Q, R, R .2 ". And" nd,. R _n 3 have, for example, those given above in group

Meanings.

Group 12

Q

Q, R. 1, R r> 2 ^~ and R ^' have, for example, those given in Group 1 above

Meanings.

Group 13

Q, R ¹ , R ² and R ^ have, for example, the meanings given above in Group 1. Group 14

Q, R ¹ , R ² and R 'have, for example, the meanings given above in Group 1

Group 15

CH,

Q, R ¹ , R ~ and R ^> have, for example, the meanings given above in Group 1

For example, 2- (2-fluoro-4-cyano-5-methoxy-phenyl) -4-methyl-5-difluoromethyl-2,4-dihydro-3H-1, 2,4-triazol-3-one and water are used as starting materials, the course of the reaction in the process according to the invention can be outlined using the following formula

The substituted aromatic nitriles to be used as starting materials in the process according to the invention for the preparation of compounds of the formula (I) are generally defined by the formula (II). In the formula (II), R ¹ , R ² and Z preferably or in particular those meanings which have already been given above in connection with the description of the compounds of the formula (I) according to the invention preferably or as particularly preferred for R ¹ , R ² and Z.

The starting materials of formula (II) are known and / or can be known

Processes are prepared (see EP-370 332, EP-648 749, DE-4 238 125, DE-4 303 376, US-5 084 084, WO 95/29168)

The process according to the invention for the preparation of the new compounds of the formula (I) is preferably carried out in the presence of a reaction auxiliary. These include water and the customary organic diluents,

Oxidizing agents, such as hydrogen peroxide or sodium chloride, as well as amidosulfonic acid

The reaction temperatures can be varied within a substantial range when carrying out the process according to the invention. In general, temperatures between 0 ° C and 150 ° C, preferably between 20 ° C and

120 ° C.

The process according to the invention is generally carried out under normal pressure. However, it is also possible to carry out the process according to the invention under increased or reduced pressure - generally between 0.1 bar and 10 bar

To carry out the process according to the invention, the starting materials are generally used in approximately equimolar amounts. However, it is also possible to use one of the components in a larger excess. The reaction is generally carried out in a suitable diluent in the presence of a reaction auxiliary and the reaction mixture is generally stirred for several hours at the required temperature. Working up is carried out by customary methods (cf. the preparation examples).

The active compounds according to the invention can be used as defoliants, desiccants, haulm killers and in particular as weed killers

Weeds in the broadest sense are understood to mean all plants that are in places growing up where they are undesirable Whether the substances according to the invention act as total or selective herbicides depends essentially on the amount used

The active compounds according to the invention can be used, for example, in the following plants

Dicotyledon weeds of the genera Sinapis, Lepidium, Gahum, Stellaπa, Matπca- πa, Anthemis, Gahnsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonu, Sesbania, Ambrosia, Solrosia, Cirs Roπppa, Rotala, Linderma, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea, Tπfolium, Ranunculus, Taraxacum

Dicotyledon cultures of the genera Gossypium, Glycine, Beta, Daucus, Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Brasica, Lactuca, Cucumis, Cucurbita

Monocot weeds of the genus Echinochloa, Setaπa, Panicum, Digitaπa,

Phleum, Poa, Festuca, Eleusine, Brachiaπa, Lohum, Bromus, Avena, Cyperus, Sorghum, Agropyron, Cynodon, Monochoπa, Fimbπstylis, Sagittaπa, Eleochaπs, Scirpus, Paspalum, Ischaemum, Sphenoclea, Agactus, Dactylusoprostus

Monocot cultures of the genera Oryza, Zea, Tπticum, Hordeum, Avena,

Seeale, sorghum, panicum, saccharum, pineapple, asparagus, alhum

However, the use of the active compounds according to the invention is by no means restricted to these genera, but extends in the same way to other plants

Depending on the concentration, the compounds are suitable for total weed control, for example on industrial and rail tracks and on paths and squares with and without tree cover. Likewise, the compounds for weed control in permanent crops, for example forest, ornamental wood, fruit, wine , Citrus, nut, banana, coffee, tea, gum, oil palm, cocoa, berry fruit and Hop plants, on ornamental and sports turf and pastures and for selective weed control in annual crops

The compounds of the formula (I) according to the invention are particularly suitable for the selective control of monocotyledon and dicotyledon weeds in onocotyledon and dicotyledon crops both in the pre-emergence and in the post-emergence

method

The active ingredients can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusting agents, pastes, soluble powders, granules, suspension emulsion concentrates, active ingredient-impregnated natural and synthetic substances and very fine encapsulations in polymers

Fabrics

These formulations are prepared in a known manner, for example by mixing the active ingredients with extenders, that is to say liquid solvents and / or solid carriers, optionally using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-producing agents.

C uenden means

If water is used as an extender, organic solvents can, for example, also be used as auxiliary solvents. Liquid solvents are essentially suitable. Aromatics such as xylene, toluene or alkyl naphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons such as chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, e.g. Petroleum fractions, mineral and vegetable oils, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and

water

Solid carrier materials are suitable. For example, ammonium salts and natural rock powders such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatorial earth and synthetic rock powders such as highly disperse silica, aluminum oxide and silicates, as solid carriers for granulates are possible: eg broken and fractionated natural pellets Rocks such as calcitum, marble, pumice, sepiolite, dolomite and synthetic granules from organic and organic flours as well as granules of organic material such as sawdust, coconut shells, corn cobs and tobacco stalks, emulsifiers and / or foam-producing agents are possible, for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol -Ether, for example alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates. Possible dispersants are, for example, lignin sulfite waste liquors and methyl cellulose

Adhesives such as carboxymethyl cellulose, natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol, polyvinyl acetate and natural ones, can be used in the formulations

Phospholipids, such as cephalins and lecithins and synthetic phosphohpides. Other additives can be mineral and vegetable oils

Dyes such as inorganic pigments, for example iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizine, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper,

Cobalt, molybdenum and zinc can be used

The formulations generally contain between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%

The active compounds according to the invention, as such or in their form, can also be used in a mixture with known herbicides for weed control, finished formulations or tank mixes being possible

Known herbicides are suitable for the mixtures, for example aceto-chlorine, acifluorfen (-sodιum), aclonifene, alachlor, alloxydιm (-sodιum), ametryne, amidochlor, amidosulfuron, asulam, atrazine, azimsulfuron, benazohn, benfuresate, bensulfuron ( -methyl), bentazone, benzofenap, benzoylprop (-ethyl), bialaphos, bifenox, bromobutide, bromofenoxime, bromoxynil, butachlor, butylates, cafenstrole, carbetamides, chloromethoxyfen, chloramben, chlorodazone, chloromuron (-ethyl), chloron Chlorsulfuron, Chlortoluron, Cinmethylin, Cinosulfuron, Clethodim, Clodinafop (-propargyl), Clomazone, Clopyrahd, Clopyrasulfuron, Clor-ansulam (-methyl), Cumyluron, Cyanazine, Cycloate, Cyclosulfamurb, Cyfyluron, Cyclofyl, Cyclofyl, Cyclofyl, Cyclofyl, Cyclofyl, Cyclofyl, Cyclofluoro, Cycloxyl, Cyclofluoro, Cycloxyl, Cyclofluoro, Cycloxyl, Cyclo 4-D, 2,4-DB, 2,4-DP, desmedipham, dialates, dicamba, dipofop (-methyl), difenzoquat, diflufenican, dimefuron, dimepiperate, dimetha- chlorine, dimethametryn, dimethenamid, dinitramine, diphenamide, diquat, dithiopyi, diuron, dymron, EPTC, esprocarb, ethalfluralm, ethametsulfuron (-methyl), ethofumesate, ethoxyfen, etobenzanide, fenoxaprop-ethyl, flamprop (-ιampropyl) -ιsopropyl-L), flamprop (-methyl), flazasulfuron, fluazιfop (-butyl), flu-metsulam, flumιclorac (-pentyl), flumioxazin, flumipropyn, fluometuron, fluorochlorodone, fluoroglycofen (-ethyl), flupacoxil, flupacoxam, flupacoxam, Flurenol, Fluπdone, Fluroxypyr, Flurprimidol, Flurtamone, Fomesafen, Glufosιnate (-ammomum), Glyphosate (-ιsopropylammonιum), Halosafen, Haloxyfop (-ethoxyethyl), Hexazino- ne, Imazamethabenz (-methyl), Imazamamazyrapyrone imazethapyr, imazosulfuron, ioxynil, Isopropahn, isoproturon, isoxaben, Isoxa- flutole, Isoxapyπfop, lactofen, lenacil, linuron, MCPA, MCPP, mefenacet, metamitron, metazachlor, methabenzthiazuron, metobenzuron, metobromuron, metolachlor, metosulam, metoxuron, metsulfuron (-methyl ), Metπbuzin, Mohnate, Monohnuron, Naproanilide, Napropamide, Neburon, Nicosulfuron, Norflurazon Orbencarb, Oryzalm, Oxadiazon, Oxyfluorfen, Paraquat, Pendimethahn, Phenmediphamam, Piperophos, Pretilachlor, Pπmιsulfuron (-methyl), Propquizilan, Propetrynil, Propetrynil, Propetrynil, Propetrynil , prosulfuron, pyrazolate, pyrazosulfuron (-ethyl), pyrazoxyfen, Pyπbuticarb, Pyπdate, Pyπthιobac (-sodιum), quinchlorac, quinmerac, Quιzalofop (ethyl), Quιzalofop (-p-tefuryl), rimsulfuron, Sethoxydi, Simazine, simetryn, Sulcotπone , Sulfentrazone, Sulfometuron (-methyl), Sulfosate, Tebutam, Tebuthiuron, Terbuthylazine, Terbutryn, Thenylchlor, Thiafluamide, Thiazopyr, Thidiazimin, Thιfensulfuron (-methyl), Thiobencarb, Tio-carbazil, Talkulfonononπ, Tralkalloxononπ, Tralkalloxononπ methyl), Tπclopyi, Tπ- diphane, Triflurahn and Tπflusulfuron

A mixture with other known active compounds, such as fungicides, insecticides, acacids, nematicides, bird repellants, plant nutrients and agents which improve soil structure, is also possible

The active compounds can be used as such, in the form of their formulations or in the use forms prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. The use is carried out in a customary manner, for example by pouring, spraying, spraying, Scatter The active compounds according to the invention can be applied both before and after the plants emerge. They can also be incorporated into the soil before sowing

The amount of active ingredient used can vary over a wide range. It depends essentially on the type of effect desired. In general, the application rates are between 1 g and 10 kg of active ingredient per hectare of soil, preferably between 5 g and 5 kg per ha

The preparation and use of the active compounds according to the invention can be seen from the examples below

Preparation Examples:

example 1

A mixture of 1.0 g (2.93 mmol) of 1 - (4-cyano-2-fluoro-5-formylphenyl) -3,6-di-hydro-2,6-dioxo-3-methyl-4 -trifluoromethyl-l (2H) -pyπmιdιn, 1 0 ml of water, 0.58 g (6 mmol) of amidosulfonic acid and 0.54 g (6 mmol) of Natπumchloπt is stirred for about 24 hours at 45 ° C. Then the mixture is mixed with ethyl acetate shaken, the organic phase separated, dried with sodium sulfate and filtered. The solvent is carefully distilled off from the filtrate in a water jet vacuum

0.90 g (82% of theory) of l- (4,5-bιs-carboxy-2-fluorophenyl) -3,6-dι- hydro-2,6-dιoxo-3-methyl-4- are obtained tπfluormethyl-l (2H) -pyπmιdιn as an amorphous residue

Example 2

COOCH, H,

A mixture of 0.80 g (2.24 mmol) l- (4,5-bιs-carboxy-2-fluorophenyl) -3,6-dι- hydro-2,6-dιoxo-3-methyl-4 -trifluoromethyl-l (2H) -pyrimidium, 0.70 g (5 mmol) of potassium carbonate, 0.64 g (5 mmol) of dimethyl sulfate and 20 ml of acetone is heated to boiling under reflux for about 20 hours. Then the mixture is concentrated in a water jet under reduced pressure , the residue taken up in 50 ml of water, mixed with 2N hydrochloric acid acidifies, then covered with 4 ml of diethyl ether and slowly diluted with petroleum ether while stirring. The product obtained in crystalline form is isolated by suction

0.38 g (42% of theory) of l- (4,5-b-methoxycarbonyl-2-fluorophenyl) - 3,6-di-hydro-2,6-di-oxo-3-methyl-4-trifluoromethyl are obtained l (2H) -pyπmιdιn melting point 141 ° C.

Example 3

4.5 g (1.0 mmol) l - (3-ethylsulfonylamino-2-fluoro-4-thiocarbamoyI-phenyl) -3,6-di-hydro-2,6-dioxo-3-methyl-4-trifluoromethyl- 1 (2H) -pyrimidine are placed in 50 ml of methylene chloride and 1.5 g (1.2 mmol) of dimethyl sulfate are added dropwise. The reaction mixture is heated under reflux for about 3 hours and at room temperature (about 20 ° C.) for a further 15 hours. After adding a further 0.5 ml of dimethyl sulfate, the mixture is heated under reflux for a further 5 hours and then concentrated in a water jet vacuum. The residue is stirred with diethyl ether and the crystalline product is isolated by suction

4.4 g (94% of theory) of 1- (3-ethylsulfonylamino-2-fluoro-4- (S-methyl-thiocarbonimidoyi-phenyl) -3,6-dihydro-2,6-dioxo-3-methyl are obtained -4-tπfluormethyl-l (2H) -pyrimidine with a melting point of 212 ° C. Analogously to preparation examples 1 to 3 and in accordance with the general description of the preparation process according to the invention, it is also possible, for example, to prepare the compounds of the formula (I) listed in table 1 below

Table 1: Examples of the compounds of the formula (I)

Starting materials of formula (II):

Example (I-l)

step 1

0.17 g (1.2 mmol) of pivalic acid chloride are stirred with a mixture of 0.50 g (1.2 mmol) of 1 - (4-cyano-2-fluoro-5-trifluoroacetylamino-phenyl) -3,6- dι- hydro-2,6-dιoxo-3-methyl-4-trifluoromethyl-l (2H) -pyπmidin, 1 ml of triethylamine and 50 ml of acetonitrile and the reaction mixture is 18 hours at 20 ° C and another 5 hours at 60 ° C stirred then concentrated in a water jet vacuum, the residue shaken with 1N hydrochloric acid / ethyl acetate, the organic phase separated, dried with sodium sulfate and filtered. The filtrate is concentrated in a water jet vacuum and the residue is purified by column chromatography (silica gel, chloroform / ethyl acetate), vol: worked up

In addition to unreacted l- (4-cyano-2-fluoro-5-trifluoroacetylamino-phenyl) -3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl-l (2H) - pyrimidine (first fraction: 0.30 g) 0.2 g (50% of theory) 1- (4-cyano-2-fluoro-5-arnino-phenyl) -3,6-di-hydro-2,6- dioxo-3-methyl-4-trifluoromethyl-1 (2H) -pyrimidine as second fraction melting point 195 ° C. Level 2

A mixture of 1.8 g (21 mmol) of methyl acrylate, 1.6 g (15.5 mmol) of t-butylnitπt, 1.6 g (12 mmol) of copper (II) chloride and 50 ml of acetonitrile is made up to approx Cooled to 0 ° C. and a solution of 3.3 g (10 mmol) l - (5-amino-4-cyano-2-fluorophenyl) -3,6-dihydro-2,6-dioxo-3-methyl- 4-trifluoromethyl-I (2H) -pyπmidine in 20 ml of acetonitrile is added dropwise at this temperature. The reaction mixture is then allowed to come to room temperature and stirred for 18 hours at this temperature. Then, after adding 20 ml of 1N hydrochloric acid with acetic acid, ethyl ester extracted, the organic phase dried with sodium sulfate and filtered. The filtrate is concentrated and the residue is worked up by column chromatography. 2.8 g (65% of theory) of l- [4-cyano-2-fiuor-5- (2-chloro- 2-methoxycarbonyl-ethyl) -phenyl] -3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl-1 (2H) -pyrimidine, melting point 46 ° C.

0.22 g of sodium hydride (60%) are cooled to 0 ° C. with stirring

Mixture of 2.0 g (4.6 mmol) l - [4-cyano-2-fluoro-5- (2-chloro-2-methoxycarbonylethyl) phenyl] -3,6-dihydro-2,6- dioxo-3-methyl-4-trifluoromethyl-l (2H) -pyrimidine and 30 ml of N, N-dimethylformamide and the reaction mixture is first 15 minutes at 0 ° C, then about 60 minutes at 20 ° C and finally 6 hours the stirred at 60 ° C. The mixture is then concentrated in a water jet vacuum, the residue is stirred with diisopropyl ether and the crystalline product is isolated by suction

1.1 g (60% of theory) of l- [4-cyano-2-fluoro-5- (2-methoxycarbonylethenyl) phenyl] -3,6-dihydro-2,6-dioxo-3- are obtained. methyl-4-trifluoromethyl-1 (2H) -pyrimidine, melting point 154 ° C. level 3

In a mixture of 8.7 g (22 mmol) l - [4-cyano-2-fluoro-5- (2-methoxycarbonyl-ethenyl) -phenyl] -3,6-dihydro-2 cooled to -70 ° C. 6-dimoxo-3-methyl-4-fluorofluoromethyl-1 (2H) -pyπmιdιn and 600 ml methylene chloride is introduced for 45 minutes. Then the cooling bath is removed and the mixture is mixed with 10 ml dimethyl sulfide after reaching room temperature (approx. 20 ° C) the phases are separated, the organic phase washed with water, dried with sodium sulfate and filtered. The filtrate is concentrated in a water jet vacuum, the residue is digested with diethyl ether and the crystalline product is isolated by suction

7.4 g (99% of theory) of l - (4-cyano-2-fluoro-5-ormylphenyl) -3,6-di-hydro-2,6-dioxo-3-methyl-4- are obtained. trιfluorrnethyl- l (2H) -pyπmιdιn from the melting point

177 ° C

Examples of use:

Example A

Pre-emergence test

Solvent 5 parts by weight acetone emulsifier 1 part by weight alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration

Seeds of the test plants are sown in normal soil. After about 24 hours, the active ingredient preparation is sprayed onto the soil, so that the desired amounts of active ingredient are applied per unit area. The concentration of the concentrated boil is chosen so that in 1 000 l of water / ha each desired amounts of active ingredient are applied

After three weeks, the degree of damage to the plants is rated in% damage compared to the development of the untreated control

Mean it

0% = no effect (like untreated control)

100% = total annihilation

In this test, for example, the compound according to production example 2 at a rate of 60 g / ha shows a very strong action against weeds such as Avena fatua (80%), Setaπa (95%), Abutilon (100%), Amaranthus (100%), Galium (95% and Sinapis (100%) Example B

Post emergence test

Solvent 5 parts by weight of acetone

Emulsifier 1 part by weight of alkylaryl polyglycol ether

Test plants which have a height of 5-15 cm are sprayed with the active compound preparation in such a way that the desired amounts of active compound are applied per unit area. The concentration of the spray is chosen so that the respectively desired amounts of active compound are applied in 1000 l of water / ha.

Mean it

0% = no effect (like untreated control) 100% = total destruction

In this test, for example, the compound according to Preparation Example 2 shows a very strong action against weeds such as Abutilon (100%), Amaranthus (100%), Galium (90%) and Sinapis (100%) at an application rate of 60 g / ha.

Claims

claims

Aromatic carbonyi compounds and their derivatives of general shapes! (1)

in which

Q represents oxygen, sulfur or imino (NH).

R represents hydrogen or halogen,

R ^{~ represents} the grouping below,

-A'-A'-A ¹

wherein

A represents a single bond, represents oxygen, sulfur, -SO-, - SO -, -, -CO- or the grouping -NR ⁴ -, in which R ^{4 represents} hydrogen, hydroxy or a radical from the series alkyl, alkoxy, aryl, Alkylsulfonyl or arylsulfonyl,

A furthermore represents an optionally substituted radical from the series alkanediyl, alkendiyi, alkindiyl, cycloalkanediyl, cycloalkendiyl or arendiyl

A ^{2 represents} a single bond, represents oxygen, sulfur, -SO-, - SO ₂ -, -CO- or the group -NR ³ -, in which R ^{5 represents} hydrogen, hydroxy or a radical from the series alkyl, aryl, alkoxy, Alkylsulfonyl or arylsulfonyl, ~>

A ~ furthermore represents an optionally substituted radical from the series alkanediyl, alkenediyi, alkindiyl, cycloalkanediyl, cycloalkenediyl or arendiyl, and

A ¹ for hydrogen, hydroxy, amino, cyano, isocyano, thiocyanato, nitio, carboxy, carbamoyl, thiocarbamoyi, sulfo,

Chlorosulfonyl, halogen or for an optionally substituted radical from the series alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, alkoxycarbonyl, dialkoxy (thιo) phosphoryl, alkenyl, alkenyloxy, alkenylamino, Λlkyhdenamino, alkenyloxycarbonyl

Alkynyl, alkynyl oxy, alkynylamino, alkynyloxycarbonyl, cycloalkyl, cycloalkyloxy, cycloalkylalkyl, cycloalkylalkoxy, cycloalkylidenamino, cycloalkyloxycarbonyl, cycloalkylalkoxycarbonyl, aryl, aryloxy, arylalkyl, arylalkoxy, aryloxycarbonyl, arylalkoxycarbonyl, heterocycloxycyclyllyloxycyclyllyl ,

R represents hydrogen, hydroxyl, mercapto, amino (in which case Q does not represent sulfur) or represents a optionally substituted radical of the alkyl, alkoxy, alkylthio or alkylamino series, and

Z represents an optionally substituted monocyclic or bicycli, saturated or unsaturated radical from the heterocyclyl series (except piperazinyl), heterocyclylamino or heterocyclic amino,

with the exception of 5-chloro-4- (l, 3-dιhydro-l, 3-dιoxo-2H-ιsoιndol-2-yl) -2-methoxy-benzoic acid ethyl ester, 5-chloro-4- (l, 3- dιhydro-l, 3-dιoxo-2H-ιso- ιndol-2-yl) -2-methoxy-benzoic acid methyl ester, 8-chloro-3- (2-chloro-5-methoxy-4-methoxycarbonyl-phenyl) -3,4-dιhydro-5-methoxy-chιnazolιn-6-carbon-acidic methyl ester

Aromatic carbonyi compounds of the general formula (I) according to

Claim 1, characterized in that Q represents oxygen, sulfur or imino (NH),

R ^{1 represents} hydrogen, fluorine, chlorine or bromine,

R ^{2 represents} the grouping below,

-A'-A ² -A ³

in which

A ¹ for a single bond, for oxygen sulfur, -SO-,

-SO ₂ -, -CO- or the grouping -NR ⁴ -, where R ⁴ fui

Hydrogen, hydroxy or a radical of the series C _r C ₄ -

Alkyl, C _j -C ₄ alkoxy, phenyl, C _| -C ₄ alkylsulfonyl or phenylsulfonyl,

A ¹ furthermore for a radical of the series C, -C ₆ -alkanedyl, C, -C ₆ -alkenediyl, C ₂ -C 6alkynediyl, C, -C ₆ -cycloalkanedyl, C, -C ₆ -cycloalkanedyl, C, -C C ₆ - cycloalkenediyl or phenylene,

A ² for a single bond, for oxygen, sulfur, -SO-,

-SO -, -, -CO- or the grouping -NR ³ -, in which R ^{3 is} hydrogen, hydroxy or a radical of the series C, -C ₄ alkyl, C _j -C _{^ j} alkoxy, phenyl, C _] -C ₄ alkylsulfonyl or phenylsulfonyl,

A ² further for each optionally by fluorine or

Chlorine-substituted radical from the series C ^ C ^ alkanediyl, C ₂ -C - alkenediyl, C ₂ -C ₆ alkynediyl, C ₃ -C ₆ -Cycloalkandιyl, C, -C ₆ - cycloalkenediyl or phenylene,

A ³ for hydrogen, hydroxyl, amino, cyano, isocyano, thiocyanato, nitro, carboxy, carbamoyl, thiocarbamoyl, sulfo,

Chlorosulfonyl, halogen or for a radical of the series alkyl, alkoxy, alkylthio, alkyl which is in each case optionally substituted by halogen, C, -C ₄ -alkoxy or C ₁ -C ₄ -alkoxιmιno sulfinyl, alkylsulfonyl, alkylamino, dialkylamino, alkoxycarbonyl or dialkoxy (thio) phosphoryl each having 1 to 6 carbon atoms in the alkyl groups,

A ^J furthermore represents a radical of the series alkenyl, alkenyloxy, alkenylamino, alkylideneamino, alkenyloxycarbonyl, alkynyl, alkynyl oxy, alkynylamino or alkynyloxycarbonyl, each with 2 to 6 carbon atoms in the alkenyl, alkylidene or alkynyl groups, optionally substituted by halogen,

A ³ furthermore for one each optionally by halogen,

Cyano, carboxy, C, -C ₄ alkyl and / or C, -C ₄ alkoxy carbonyl substituted radical from the series cycloalkyl, cycloalkyloxy, cycloalkylalkyl, cycloalkylalkoxy, cycloalkylidene amino, cycloalkyloxycarbonyl or cycloalkylalkoxycarbonyl, each with 3 to 6 carbon atoms in the

Cycloalkyl groups and optionally 1 to 4 carbon atoms in the alkyl groups,

A further for each optionally by nitro, cyano, carboxy, halogen, C, -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C _] -C ₄ alkyloxy, C, -C ₄ haloalkyloxy and / or C , -C ₄ -

Alkoxy-carbonyl-substituted radical of the series phenyl, phenyloxy, phenyl-C _] -C ₄ -alkyl, phenyl-C _r C ₄ -alkoxy, phenyloxycarbonyl or phenyl-C ₁ -C ₄ -alkoxycarbonyl, (in each case optionally fully or partially hydrogenated) Pyrrolyl, pyrazolyl, imidazolyl, triazolyl, furyl, thienyl,

Oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, pyrimidinyl, triazinyl, pyrazolyl-C, -C ₄ -alkyl, furyl-C _r C ₄ -alkyl, thienyl-C _r C ₄ -alkyl, oxazolyl- C _j -C ₄ -alkyl, isoxazole-C, -C ₄ -alkyl, thiazole-C, -C ₄ -alkyl, pyridinyl-C _r C ₄ -alkyl, pyrimidinyl-C _r C ₄ -alkyl, pyrazolyl-methoxy, furylmethoxy, represents perhydropyranylmethoxy or pyridylmethoxy, R ^{3 represents} hydrogen, hydroxyl, mercapto, amino (in which case Q does not represent sulfur) or a radical which is optionally substituted by hydroxy, cyano, halogen, C, -C ₄ -alkoxy or C _r C ₄ -alkoxycarbonyl Series of alkyl, alkoxy, alkylthio or alkylamino, each with 1 to 6 carbon atoms in the

Alkylg ppen stands, and

Z represents a respective monocyclic or bicyclic, saturated or unsaturated radical from the heterocyclyl series (except piperazinyl), heterocyclylamino or heterocyclyhmino each having 2 to 6 carbon atoms and 1 to 4 nitrogen atoms in the heterocyclic ring system, which optionally also contains an oxygen or sulfur atom and / or optionally up to three groupings from the series -CO-, -CS-, -SO- and / or SO -, -, and which is optionally substituted by one or more groupings from the series nitro, hydroxy, amino,

Cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, C _] -C ₆ alkyl (which in turn is optionally substituted by halogen or C _j -C ₄ alkoxy), C ₂ -C ₆ alkenyl or C ₂ -C ₆ alkynyl (which in turn are each optionally substituted by halogen), CC ₈ -alkoxy or C, -C ₆ -alkoxy-carbonyl (which in turn are each optionally substituted by halogen or C, -C ₄ -alkoxy), C -, - C -Alkenyloxy or C -, - C -alkionyloxy (which in turn are each optionally substituted by halogen), C, -C ₆ -alkylthio, C ₂ -C ₆ -alkenylthio or C ₂ -C ₆ -alkionylthio (which in turn, if appropriate are substituted by halogen),

CC ₆ -Alkylamιno or Dι- (C _] -C ₄ -alkyl) -amιno, C ₃ -C ₆ -cycloalkyl or C ₃ -C ₆ -cycloalkyl-C _r C ₄ -alkyl (which in turn in each case optionally by halogen and / or C 1 -C ₄ -alkyl), phenyl, phenoxy, phenylthio, phenylsulfinyl, phenylsulfonyl or phenylamino (which in turn are each optionally substituted by nitro,

Cyano, halogen, C _] -C ₄ alkyl, C _] -C ₄ haloalkyl, C _j -C _j alkyloxy, C _r C ₄ haloalkyloxy and / or C ^ C. _j -alkoxy-carbonyl are substituted),

with the exception of 5-chloro-4- (l, 3-dιhydro-l, 3-dιoxo-2H-ιsoιndol-2-yl) -2-methoxy-benzoic acid ethyl ester, 5-chloro-4- (1, 3- dιhydro- 1, 3-dιoxo-2H-ιso- methyl indol-2-yl) -2-methoxybenzoate, 8-chloro-3- (2-chloro-5-methoxy-4-methoxycarbonylphenyl) -3,4-dihydro-5-methoxyquinazoline -6- carboxylic acid methyl ester

Aromatic carbonyi compounds of the general formula (I) according to Claim 1, characterized in that

Q represents oxygen, sulfur or imino (NH),

R ^{1 represents} hydrogen, fluorine or chlorine,

R ^{2 represents} the grouping below,

-A ^! -A ² -A ³

in which

A ¹ for a single bond, for oxygen, sulfur, -SO-,

-SO ₂ -, -CO- or the grouping -NR ⁴ -, where R ^{4 is}

Hydrogen, hydroxy or a residue of the series methyl,

Is ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylsulfonyl or ethylsulfonyl,

A ¹ for a radical of the series methylene, ethane-1, 1-diyl, ethane-1, 2-diyl, propane-1, 1-diyl, propane-1, 2-diyl, propane-1,3-diyl, Ethene-1,2-diyl, propene-1,2-diyl, propene-1,3-diyl, ethyne-1,2-diyl, propyne-1,2-diyl or propyne-1,3-diyl,

A ² for a single bond, for oxygen, sulfur, -SO-, -

SO ₂ -, -CO- or the grouping -NR ³ -, in which R ^{5 represents} hydrogen, hydroxy or a radical of the series methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, Methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl or phenylsulfonyl,

A "also for a radical of the series methylene, ethane-1, 1-diyl, ethane-1,2-diyl, propane-1, 1-diyl, propane-1,2-diyl, propane-1,3- diyl, ethene-1,2-diyl, propene-1,2-diyl, propene-1,3-diyl, ethyne-1,2-diyl, propyne-1,2-diyl or propyne-1,3-diyl ,

A ³ for hydrogen, hydroxy, amino, cyano, nitro, carboxy,

Carbamoyl, sulfo, fluorine, chlorine, bromine, for a

5 optionally by fluorine, chlorine, methoxy, ethoxy,

Methoximino or ethoximino substituted radical of the series methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-, i-, s- or t-pentyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, n-, i-, s- or t-pentyloxy, methylthio,

10 ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio,

Methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino, diethylamino, Methoxy

15 carbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl,

Dimethoxyphosphoryl, diethoxyphosphoryl, dipropoxyphosphoryl or diisopropoxyphosphoryl,

A ³ further for each optionally by fluorine or

Chlorine-substituted radical from the propenyl, butenyl,

20 propenyloxy, butenyloxy, propenylamino, butenylamino,

Propylidene amino, butylidene amino, propenyloxycarbonyl, butenyloxycarbonyl, propynyl, butynyl, propynyloxy, butynyloxy, propynylamino, butynylamino, propynyloxycarbonyl or butynyloxy carbonyl,

25 A further for each optionally by fluorine,

Chlorine, cyano, carboxy, methyl, ethyl, n- or i-propyl, methoxycarbonyl or ethoxycarbonyl substituted radical from the series cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy,

30 cyclohexyloxy, cyclopropylmethyl, cyclobutylmethyl,

Cyclopentylmethyl, Cyclohexylmethyl, Cyclo-propyl-methoxy, Cyclobutylmethoxy, Cyclopentylmethoxy, Cyclohexylmethoxy, Cyclopentylidenamino, Cyclohexylidenamino, Cyclopentyloxycarbonyl, Cyclohexyloxycarbonyl, Cyclo- pentylmethoxycarbonyl or cyclohexylmethoxycarbonyl,

A ³ furthermore for one in each case optionally by nitro,

Cyano, carboxy, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, trifluoromethyl, methoxy, ethoxy, n- or i-

Propoxy, difluoromethoxy, trifluoromethoxy, methoxycarbonyl and / or ethoxycarbonyl substituted radical from the series phenyl, phenyloxy, benzyl, phenylethyl, benzyloxy, phenyloxycarbonyl, benzyloxycarbonyl, (in each case fully or partially hydrogenated) pyrrolyl, pyrazolyl,

Imidazolyl, triazolyl, furyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyπdinyl, pyrimidinyl, tπazinyl, pyrazolylmethyl, furylmethyl, thienylmethyl, oxazolylethyl, pyridomethylmethyl, isoxazylmethylmethyl, isoxazolmethylmethyl Furylmethoxy or pyridylmethoxy,

R ^{3 represents} hydrogen, hydroxy, mercapto, amino (in which case Q does not represent sulfur) or one in each case, if appropriate

Hydroxy, cyano, fluorine, chlorine, methoxy, ethoxy, methoxycarbonyl or ethoxycarbonyl-substituted radical of the series methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylamino, ethyliamino, n- or i-propylamino, and

Z represents a respective monocyclic or bicyclic, saturated or unsaturated radical from the heterocyclyl series (exception: piperazinyl),

Heterocyclylamino or heterocyclylimino, each with 2 to 5 carbon atoms and 1 to 3 nitrogen atoms in the heterocyclic ring system, which optionally additionally contains an oxygen or sulfur atom and / or optionally up to two groups from the series -CO-, -CS-, -SO - and / or SO -, -, and which is optionally substituted by one or more groups from the series nitro, hydroxyl, amino, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, (which are in turn optionally substituted by fluorine, chlorine, methoxy or ethoxy), propenyl, butenyl, propynyl or butinyl (which in turn are each optionally substituted by fluorine or chlorine), methoxy, ethoxy, n- or i-propoxy, n-, 1- , s- or t-butoxy, methoxycarbonyl or ethoxycarbonyl (which in turn are each optionally substituted by fluorine, chloro, methoxy or ethoxy), propenyloxy, butenyloxy, propyloxy or butynyloxy (which in turn are optionally substituted by fluorine or chloro), methylthio, ethylthio , n- or i-propylthio, n-, I-, s- or t-butylthio, propenylthio, butenylthio, propynylthio or butynylthio

(which in turn are optionally substituted by fluorine or chlorine), methylamino, ethylamino, n- or l-propylamino, n-, l-, s- or t-butylamino, dimethylamino or diethylamino, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropyl - methyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl (which in turn are each optionally substituted by fluorine, chlorine, methyl, ethyl, n- or i-propyl), phenyl, phenoxy, phenylthio, phenylsulfinyl, phenylsulfonyl or phenylamino (which in turn each optionally substituted by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, Tπ-fluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, Tπfluormethoxy, methoxycarbonyl or ethoxycarbonyl

with the exception of 5-chloro-4- (l, 3-dιhydro-l, 3-dιoxo-2H-ιsoιndol-2-yl) -2-methoxy-benzoic acid ethyl ester, 5-chloro-4- (l, 3- dιhydro-l, 3-dιoxo-2H- ιsoιndol-2-yl) -2-methoxy-benzoic acid methyl ester, 8-chloro-3- (2-chloro-5-methoxy-4-methoxycarbonyl-phenyl) -3.4 -dιhydro-5-methoxy-chιnazolιn-6-carboxylic acid methyl ester

Process for the preparation of aromatic carbonyi compounds of the general formula (I) in which

1 0 ^

R, R ", R, Q and Z have the meanings given in Claim 1,

characterized in that aromatic nitriles of the formula (II)

in which

R, 1, R _D 2 ~ and Z have the meanings given above,

with water, hydrogen sulfide or ammonia and the resulting substituted aromatic carboxylic acids or their derivatives of the general formula (Ia)

in which

Q, R 1, R _D 2 and Z have the meanings given above, converted into substituted aromatic carbonyl compounds or their derivatives according to the above definition of the compounds of formula (I) by customary methods

Herbicidal agents, characterized in that they contain at least one aromatic carbonyl compound of the formula (I) according to Claim 1

Process for combating unwanted plants, characterized in that aromatic carbonyi compounds of the formula (I) according to Claim 1 are allowed to act on undesired plants and / or their habitat

Use of aromatic carbonyi compounds of formula (I) according to claim 1 for combating undesirable plants

Process for the preparation of herbicidal compositions, characterized in that aromatic carbonyi compounds of the formula (I) according to Claim 1 are mixed with extenders and / or surface-active substances